4-((3-(2-((3-Chloro-4-fluorophenyl)sulfonamido)ethyl)phenyl)carbamoyl)phenyl diethylcarbamate

ID: ALA4468229

PubChem CID: 155532966

Max Phase: Preclinical

Molecular Formula: C26H27ClFN3O5S

Molecular Weight: 548.04

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN(CC)C(=O)Oc1ccc(C(=O)Nc2cccc(CCNS(=O)(=O)c3ccc(F)c(Cl)c3)c2)cc1

Standard InChI:  InChI=1S/C26H27ClFN3O5S/c1-3-31(4-2)26(33)36-21-10-8-19(9-11-21)25(32)30-20-7-5-6-18(16-20)14-15-29-37(34,35)22-12-13-24(28)23(27)17-22/h5-13,16-17,29H,3-4,14-15H2,1-2H3,(H,30,32)

Standard InChI Key:  IYRWKZBOHCLUDG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 37 39  0  0  0  0  0  0  0  0999 V2000
    3.7475   -1.2918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1602   -2.0017    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5687   -1.2893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5271   -2.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5260   -3.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2340   -3.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9437   -3.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9409   -2.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2323   -1.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8193   -1.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1117   -2.3982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6521   -3.6244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3591   -3.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0675   -3.6222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3578   -2.3975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0688   -4.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7745   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4829   -3.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7771   -4.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8191   -1.1723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4039   -1.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4074   -1.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7004   -0.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9918   -1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9946   -1.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7022   -2.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2885   -2.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5792   -1.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8730   -2.4105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4576   -2.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489   -2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0467   -2.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0536   -3.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7685   -3.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4677   -3.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3356   -2.0239    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3502   -3.6587    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  4 10  1  0
 10 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 16 19  1  0
 10 20  2  0
 11 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29  2  1  0
  2 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
 32 36  1  0
 33 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4468229

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 548.04

Molecular Weight (Monoisotopic): 547.1344

AlogP: 5.09

#Rotatable Bonds: 10

Polar Surface Area: 104.81

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.09

CX Basic pKa: ┄

CX LogP: 5.09

CX LogD: 5.08

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.37

Np Likeness Score: -1.82

References

1. Summer SL, Kell SA, Zhu Z, Moore R, Liotta DC, Myers SJ, Koszalka GW, Traynelis SF, Menaldino DS..  (2019)  Di-aryl Sulfonamide Motif Adds π-Stacking Bulk in Negative Allosteric Modulators of the NMDA Receptor.,  10  (3): [PMID:30891121] [10.1021/acsmedchemlett.8b00395]

Source

Source(1):

• Scientific Literature